Tetrahedron

Synthetic studies on biologically active natural products by a chemicoenzymatic approach: Enantioselective synthesis of C-and N-nucleosides, showdomycin, 6- …

M Ohno, Y Ito, M Arita, T Shibata, K Adachi, H Sawai

Index: Ohno, Masaji; Ito, Yukishige; Arita, Masafumi; Shibata, Tomoyuki; Adachi, Kunitomo; Sawai, Hiroaki Tetrahedron, 1984 , vol. 40, # 1 p. 145 - 152

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Citation Number: 67

Abstract

An efficient synthesis of C-and N-nucleosides has been developed in an enantioselective and stereocontrolled manner starting from Diels-Alder adduct of furan and dimethyl acetylenedicarboxylate by chemicoenzymatic strategy. The symmetric unsaturated dimethyl esters 2 and 3 were almost quantitatively hydrolysed with pig liver esterase to yield half- esters 4 and 5 with reasonably high optical yields. Decarboxylative ozonolysis of the chiral ...